WO2014210166A1 - Capteurs de sulfure d'hydrogène à base d'époxyde - Google Patents

Capteurs de sulfure d'hydrogène à base d'époxyde Download PDF

Info

Publication number
WO2014210166A1
WO2014210166A1 PCT/US2014/044114 US2014044114W WO2014210166A1 WO 2014210166 A1 WO2014210166 A1 WO 2014210166A1 US 2014044114 W US2014044114 W US 2014044114W WO 2014210166 A1 WO2014210166 A1 WO 2014210166A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen
alkyl
group
aryl
heteroaryl
Prior art date
Application number
PCT/US2014/044114
Other languages
English (en)
Inventor
Jennifer L. SORRELLS
Nestor U. SORIANO, Jr.
Original Assignee
Ecolab Usa Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ecolab Usa Inc. filed Critical Ecolab Usa Inc.
Publication of WO2014210166A1 publication Critical patent/WO2014210166A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/38—Removing components of undefined structure
    • B01D53/44—Organic components
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/46—Removing components of defined structure
    • B01D53/48—Sulfur compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/46—Removing components of defined structure
    • B01D53/48—Sulfur compounds
    • B01D53/52—Hydrogen sulfide
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • C10G29/22—Organic compounds not containing metal atoms containing oxygen as the only hetero atom
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
    • C10L3/10—Working-up natural gas or synthetic natural gas
    • C10L3/101—Removal of contaminants
    • C10L3/102—Removal of contaminants of acid contaminants
    • C10L3/103—Sulfur containing contaminants
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/202—Alcohols or their derivatives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/60—Additives
    • B01D2252/606—Anticorrosion agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/60—Additives
    • B01D2252/608—Antifoaming agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/60—Additives
    • B01D2252/61—Antifouling agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2256/00—Main component in the product gas stream after treatment
    • B01D2256/24—Hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/30—Sulfur compounds
    • B01D2257/304—Hydrogen sulfide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/30—Sulfur compounds
    • B01D2257/306—Organic sulfur compounds, e.g. mercaptans
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/05—Biogas
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1033—Oil well production fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/02—Absorbents, e.g. in the absence of an actual absorbent column or scavenger
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/14—Injection, e.g. in a reactor or a fuel stream during fuel production
    • C10L2290/141—Injection, e.g. in a reactor or a fuel stream during fuel production of additive or catalyst

Definitions

  • the present disclosure relates generally to scavengers of sulfur-based species, and more particularly to epoxide compounds and compositions as scavengers of hydrogen sulfide and/or mercaptans.
  • a method of sweetening a fluid or gas comprising treating the fluid or gas with an effective amount of a composition comprising a compound of formula (I),
  • X is selected from the group consisting of -OH, -SH, and -NHR ;
  • R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, cycloalkyl, and -C(0)R ;
  • R 7 is selected from the group consisting of -OR 15 , -SR 16 , -NR 17 R 18 , hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
  • R 15 , R 16 , R 17 , and R 18 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
  • R a , R b , R c , R d , R e , R f , and R g are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl; or R d and R f together with the carbon atoms to which they are attached form an aryl or a heteroaryl, provided that R e and R g are absent when R d and R f together with the carbon atoms to which they are attached form an aryl or a heteroaryl; and
  • n is 0 or 1 ; wherein said alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl are each independently, at each occurrence, substituted or unsubstituted with one or more suitable substituents.
  • X can be -OH.
  • R a , R b , R c , R d , R e , R f , and R g can each independently be selected from the group consisting of hydrogen, substituted or unsubstituted Q-Qo-alkyl, fluoro, bromo, and iodo.
  • Compounds of Formula I can have substituents where X is -OH; R a is hydrogen or substituted or unsubstituted alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen or substituted or unsubstituted alkyl; R e is hydrogen; and n is 0.
  • Compounds of Formula I can have substituents where X is -OH; R a is hydrogen or unsubstituted CrCio-alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen or unsubstituted Q-Qo-alkyl; R e is hydrogen; and n is 0.
  • Compounds of Formula I can have substituents where X is -OH; R a is hydrogen or substituted or unsubstituted alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is hydrogen or substituted or unsubstituted alkyl; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have substituents where R a , R b , and R c are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl; R d and R f together with the carbon atoms to which they are attached form an aryl group; R e is absent; R g is absent; and n is 1.
  • Compounds of Formula I can have substituents where X is -OH; R a is hydrogen; R b is hydrogen; R c is hydrogen; R d and R f together with the carbon atoms to which they are attached form a phenyl group, optionally having one to four suitable substituents in addition to the -OH; R e is absent; R g is absent; and n is 1.
  • Compounds of Formula I can have substituents where X is -OH; R a is - (CH 2 )7-C(0)OR x , wherein R x is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl, wherein said alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl are each independently, at each occurrence, substituted or unsubstituted with one or more suitable substituents; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is -(CH 2 ) 5 CH 3 ; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have substituents where X is -OH; R a is - (CH 2 ) 7 -C(0)OR x , wherei x is
  • Compounds of Formula I can have substituents where X is -OH; R a is - (CH 2 ) 7 -C(0)OR x , wherein R x is
  • Compounds of Formula I can have substituents where the compound of formula (I) is selected from the group consisting of:
  • composition containing one or more compounds of Formula I can further include one or more additional components, each component independently selected from the group consisting of asphaltene inhibitors, paraffin inhibitors, corrosion inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, hydrogen sulfide scavengers, gas hydrate inhibitors, biocides, pH modifiers, surfactants, and solvents.
  • each component independently selected from the group consisting of asphaltene inhibitors, paraffin inhibitors, corrosion inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, hydrogen sulfide scavengers, gas hydrate inhibitors, biocides, pH modifiers, surfactants, and solvents.
  • the composition can also include at least one solvent.
  • the solvent can be an alcohol, a hydrocarbon, a ketone, an ether, an aromatic, an amide, a nitrile, a sulfoxide, an ester, an aqueous system, or a combination thereof.
  • the composition can also comprise a surfactant.
  • the surfactant can be a cocodimethylamine oxide surfactant.
  • the composition can include about 50 wt % of one or more compounds of Formula I, 0-20 wt % cocodimethylamine oxide, and 30-50 wt % methyl carbitol.
  • the composition can include about 50 wt % of one or more compounds of formula (I), about 3 wt % cocodimethylamine oxide, and about 47 wt % methyl carbitol.
  • composition comprising compounds of Formula I scavenges hydrogen sulfide and/or mercaptans from the fluid or gas.
  • the fluid or gas can be produced or used in the production, transportation, storage, and/or separation of crude oil or natural gas.
  • the fluid or gas can be produced or used in a coal-fired process, a waste-water process, a farm, a slaughter house, a land-fill, a municipality waste-water plant, a coking coal process, or a biofuel process.
  • composition can comprise a mixture of compounds of Formula I.
  • a method of sweetening a fluid or gas comprising treating the fluid or gas with an effective amount of a composition comprising one or more compounds of formula (II),
  • R is independently, at each occurrence, selected from the group consisting of hydrogen and a moiety comprising an a- or ⁇ -functionalized epoxide, said a- or ⁇ - functionalization selected from the group consisting of -OH, -SH, and -NHR 23 , wherein at least one R group is a moiety comprising said a- or ⁇ -functionalized epoxide;
  • R 23 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, cycloalkyl, and -C(0)R 27 ;
  • R 27 is selected from the group consisting of -OR 35 , -SR 36 , -NR 37 R 38 , hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
  • R 35 , R 36 , R 37 , and R 3 J 8 O are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
  • R', R", R'", R s , and R 1 are each independently, at each occurrence, selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl; y is independently, at each occurrence, an integer selected from 0 to 6; and z is an integer selected from 1 to 20; wherein said alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl are each independently, at each occurrence, substituted or unsubstituted with one or more suitable substituents.
  • y is 0 at each occurrence
  • the composition can further include one or more additional components, each component independently selected from the group consisting of asphaltene inhibitors, paraffin inhibitors, corrosion inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, hydrogen sulfide scavengers, gas hydrate inhibitors, biocides, pH modifiers, surfactants, and solvents.
  • each component independently selected from the group consisting of asphaltene inhibitors, paraffin inhibitors, corrosion inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, hydrogen sulfide scavengers, gas hydrate inhibitors, biocides, pH modifiers, surfactants, and solvents.
  • the composition can also include at least one solvent.
  • the solvent can be an alcohol, a hydrocarbon, a ketone, an ether, an aromatic, an amide, a nitrile, a sulfoxide, an ester, an aqueous system, or a combination thereof.
  • the composition can further comprise a surfactant.
  • the surfactant can be a cocodimethylamine oxide surfactant.
  • the composition includes about 50 wt % of one or more compounds of Formula II, 0-20 wt % cocodimethylamine oxide, and 30-50 wt % methyl carbitol.
  • the composition includes about 50 wt % of one or more compounds of formula (II), about 3 wt % cocodimethylamine oxide, and about 47 wt % methyl carbitol.
  • composition comprising compounds of Formula II scavenges hydrogen sulfide and/or mercaptans from the fluid or gas.
  • the fluid or gas can be produced or used in the production, transportation, storage, and/or separation of crude oil or natural gas.
  • the fluid or gas can be produced or used in a coal-fired process, a waste-water process, a farm, a slaughter house, a land-fill, a municipality waste-water plant, a coking coal process, or a biofuel process.
  • composition can comprise a mixture of compounds of Formula II.
  • Figure 1 depicts scavenging of 1 -propyl mercaptan using 3- hydroxypropylene oxide.
  • Figure 2 depicts scavenging of 1 -propyl mercaptan, 2-propyl mercaptan, butyl mercaptan, benzyl thiol, and ethanol thiol using 3-hydroxypropylene oxide.
  • Figure 3 depicts scavenging of 1 -propyl mercaptan, 2-propyl mercaptan, butyl mercaptan, benzyl thiol, and ethanol thiol using 3-hydroxypropylene oxide in the absence or presence of a surfactant.
  • the compounds and compositions are particularly useful in the removal of hydrogen sulfide and/or mercaptans from crude oil based, natural gas based, and coal based products, processes, and refinery streams.
  • the compounds and compositions are applicable to both upstream and downstream processes.
  • the scavenging compounds and compositions optionally blended with one or more solvents and/or one or more surfactants (e.g.,
  • cocodimethyl amine oxide surfactant are useful in a wide range of climates and under a wide range of process conditions.
  • the compounds and compositions disclosed herein are able to remove hydrogen sulfide and/or mercaptans from fuels (e.g., finished fuels) without hazing or clouding of the fuel.
  • fuels e.g., finished fuels
  • Other advantages of the disclosed compounds and compositions include that the compounds and compositions are non- nitrogen based; pass all standard American Society for Testing and Materials (ASTM) and Universal Oil Products (UOP) tests for mercaptans; are non-aqueous based; and are small molecules with low volatility. Additionally, the scavenged product diols possess low volatility, easing sequestration and removal from treated fluids and gases.
  • the unexpected superior scavenging ability of the disclosed a- or ⁇ -functionalized epoxide compounds results from intramolecular acid catalysis of the epoxide by the adjacent a- or ⁇ - functionality.
  • the internal acid catalysis weakens the epoxide C-0 bond and promotes nucleophilic addition of mercaptans and/or hydrogen sulfide to the epoxide.
  • the a- or ⁇ -functionalization activates the epoxide for nucleophilic addition by serving as a hydrogen bond donor.
  • alkyl refers to a linear or branched
  • alkenyl refers to a straight or branched hydrocarbon radical, preferably having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 39, 30, 31, or 32 carbons, and having one or more carbon-carbon double bonds.
  • Alkenyl groups include, but are not limited to, ethenyl, 1-propenyl, 2-propenyl (allyl), iso-propenyl, 2-methyl-l- propenyl, 1-butenyl, and 2-butenyl. Alkenyl groups can be unsubstituted or substituted by one or more suitable substituents, as defined above.
  • Alkylcarbonylamino refers to groups such as acetamide.
  • cycloalkyl refers to a mono, bicyclic or tricyclic carbocyclic radical (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclopentenyl, cyclohexenyl,
  • Cycloalkyl groups can be unsubstituted or substituted by one or more suitable substituents, preferably 1 to 5 suitable substituents, as defined above.
  • halo or halogen
  • halo refers to a fluoro, chloro, bromo or iodo radical.
  • heteroaryl refers to a monocyclic, bicyclic, or tricyclic aromatic heterocyclic group containing one or more heteroatoms selected from O, S and N in the ring(s).
  • Heteroaryl groups include, but are not limited to, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thienyl, furyl, imidazolyl, pyrrolyl, oxazolyl (e.g., 1,3-oxazolyl, 1,2-oxazolyl), thiazolyl (e.g., 1 ,2-thiazolyl, 1,3- thiazolyl), pyrazolyl, tetrazolyl, triazolyl (e.g., 1,2,3-triazolyl, 1,2,4-triazolyl), oxadiazolyl (e.g., 1,2,3-oxadiazolyl), thiadiazol
  • Heteroaryl groups can be unsubstituted or substituted by one or more suitable substituents, preferably 1 to 5 suitable substituents, as defined above.
  • the term "heterocycle,” as used herein, refers to a monocyclic, bicyclic, or tricyclic group containing 1 to 4 heteroatoms selected from N, O, S(0) n , P(0) n , PR Z , NH or NR Z , wherein R z is a suitable substituent.
  • Heterocyclic groups optionally contain 1 or 2 double bonds.
  • Heterocyclic groups include, but are not limited to, azetidinyl, tetrahydrofuranyl, imidazolidinyl, pyrrolidinyl, piperidinyl, piperazinyl, oxazolidinyl, thiazolidinyl, pyrazolidinyl, thiomorpholinyl,
  • tetrahydrodiazinyl oxazinyl, oxathiazinyl, indolinyl, isoindolinyl, quinuclidinyl, chromanyl, isochromanyl, and benzoxazinyl.
  • Examples of monocyclic saturated or partially saturated ring systems are tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, imidazolidin-l-yl, imidazolidin-2-yl, imidazolidin-4-yl, pyrrolidin-l-yl, pyrrolidin- 2-yl, pyrrolidin-3-yl, piperidin-l-yl, piperidin-2-yl, piperidin-3-yl, piperazin-l-yl, piperazin-2-yl, piperazin-3-yl, l,3-oxazolidin-3-yl, isothiazolidine, l,3-thiazolidin-3- yl, l,2-pyrazolidin-2-yl, 1,3-pyrazolidin-l-yl, thiomorpholin-yl, 1,2- tetrahydrothiazin-2-yl, 1 ,3-tetrahydrothiazin-3-
  • hydroxy refers to an -OH group.
  • counterion means a halide (e.g., fluoride, chloride, bromide, iodide), a carboxylate anion, such as selected from deprotonation of mineral acid, acrylic acid, acetic acid, methacrylic acid, glycolic acid, thioglycolic acid, propionic acid, butyric acid, and the like, or any other anionic constituent that satisfies the charge balance necessary to form a neutral molecule.
  • halide e.g., fluoride, chloride, bromide, iodide
  • carboxylate anion such as selected from deprotonation of mineral acid, acrylic acid, acetic acid, methacrylic acid, glycolic acid, thioglycolic acid, propionic acid, butyric acid, and the like, or any other anionic constituent that satisfies the charge balance necessary to form a neutral molecule.
  • sweetening can refer to a process that removes sulfur species from a gas or liquid.
  • the sulfur species can include hydrogen sulfide and mercaptans.
  • sour gas can refer to a gas that includes significant amounts of sulfur species, such as hydrogen sulfide and/or mercaptans.
  • sour liquid or "sour fluid,” as used herein, can refer to a liquid that includes significant amounts of sulfur species, such as hydrogen sulfide and/or mercaptans.
  • Compounds of the invention include scavengers of sulfur-based species, such as hydrogen sulfide and mercaptans.
  • the compounds can be particularly useful for scavenging of hydrogen sulfide and/or mercaptans from liquids and gases found in the oil, gas, and/or coal industries.
  • the compounds can be alpha- or beta- functionalized epoxides.
  • R 7 is selected from the group consisting of -OR 15 , -SR 16 , -NR 17 R 18 , hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
  • R 15 , R 16 , R 17 , and R 18 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
  • R a , R b , R c , R d , R e , R f , and R g are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl; or R d and R f together with the carbon atoms to which they are attached form an aryl or a heteroaryl, provided that R e and R g are absent when R d and R f together with the carbon atoms to which they are attached form an aryl or a heteroaryl; and n is 0 or 1 ; wherein said alkyl, alkenyl, alkynyl, aryl,
  • R e and R g are absent.
  • Compounds of Formula I can have X be -SH.
  • Compounds of Formula I can have X be -NHR 3 wherein R 3 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, cycloalkyl, or -C(0)R .
  • R 3 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, cycloalkyl, or -C(0)R .
  • X is -NHR 3 wherein R 3 is hydrogen.
  • Compounds of Formula I can have X be -NHR 3 wherein R 3 is d -alkyl, C 2 -alkyl, C 3 -alkyl, C 4 -alkyl, C 5 -alkyl, or C 6 -alkyl.
  • Compounds of Formula I can also have R a , R b , R c , R d , R e , R f , and R g each independently be selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and halogen.
  • Compounds of Formula I can further have R a , R b , R c , R d , R e , R f , and R g each independently be selected from the group consisting of hydrogen, substituted or unsubstituted CrCio-alkyl, fluoro, bromo, and iodo.
  • Compounds of Formula I can have R a , R b , and R c each independently be selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl; R d and R f together with the carbon atoms to which they are attached form an aryl group (e.g., phenyl); R e is absent; R g is absent; and n is i.
  • Compounds of Formula I can have groups where X is -OH; R a is hydrogen; R b is hydrogen; R c is hydrogen; R d is substituted or unsubstituted alkyl; R e is hydrogen; and n is 0.
  • X is -OH; R a is hydrogen or substituted or unsubstituted alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; and n is 0.
  • X is -OH; R a is substituted or unsubstituted alkyl; R b is hydrogen; R c is hydrogen; R d is substituted or
  • R e is hydrogen; and n is 0.
  • X is -OH; R a is substituted or unsubstituted alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; and n is 0.
  • Compounds of Formula I can have structures where X is -OH; R a is hydrogen or unsubstituted C Cio-alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen or unsubstituted CrCio-alkyl; R e is hydrogen; and n is 0. [0082] Compounds of Formula I can also have structures where X is -OH; R A is hydrogen; R B is hydrogen; R C is hydrogen; R D is hydrogen or unsubstituted Q-CK T alkyl; R E is hydrogen; and n is 0.
  • compounds of Formula I can have structures where X is - OH; R A is hydrogen; R B is hydrogen; R C is hydrogen; R D is unsubstituted Q-CK T alkyl; R E is hydrogen; and n is 0.
  • Compounds of Formula I can have structures where X is -OH; R A is hydrogen or unsubstituted CrCio-alkyl; R B is hydrogen; R C is hydrogen; R D is hydrogen; R E is hydrogen; and n is 0.
  • compounds of Formula I can have structures where X is -OH; R A is unsubstituted CrQo-alkyl; R B is hydrogen; R C is hydrogen; R D is unsubstituted Ci-Cio-alkyl; R E is hydrogen; and n is 0.
  • Compounds of Formula I can have structures where X is -OH; R A is unsubstituted Q-Qo-alkyl; R B is hydrogen; R C is hydrogen; R D is hydrogen; R E is hydrogen; and n is 0.
  • compounds of Formula I can have structures where X is -OH; R A is hydrogen or substituted or unsubstituted alkyl; R B is hydrogen; R C is hydrogen; R D is hydrogen; R E is hydrogen; R F is hydrogen or substituted or unsubstituted alkyl; R G is hydrogen; and n is 1.
  • compounds of Formula I can have structures where X is - OH; R A is hydrogen; R B is hydrogen; R C is hydrogen; R D is hydrogen; R E is hydrogen; R F is substituted or unsubstituted alkyl; R G is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R A is hydrogen or substituted or unsubstituted alkyl; R B is hydrogen; R C is hydrogen; R D is hydrogen; R E is hydrogen; R F is hydrogen; R G is hydrogen; and n is 1.
  • compounds of Formula I can have structures where X is -OH; R A is substituted or unsubstituted alkyl; R B is hydrogen; R C is hydrogen; R D is hydrogen; R E is hydrogen; R F is substituted or unsubstituted alkyl; R G is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is substituted or unsubstituted alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is hydrogen; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is hydrogen; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is hydrogen; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is hydrogen or unsubstituted CrCio-alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is hydrogen or unsubstituted Q-Qo-alkyl; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is hydrogen; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is hydrogen or unsubstituted Q-Qo-alkyl; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is hydrogen; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is unsubstituted CrCio-alkyl; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is hydrogen or unsubstituted Q-Qo-alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is hydrogen; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is unsubstituted Q-Qo-alkyl; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is unsubstituted Q-Qo-alkyl; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is hydrogen; R b is hydrogen; R c is hydrogen; R d and R f together with the carbon atoms to which they are attached form a phenyl group, optionally having one to four suitable substituents in addition to the -OH; R e is absent; R g is absent; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is - (CH 2 )7-C(0)OR x , wherein R x is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl, wherein said alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl are each independently, at each occurrence, substituted or unsubstituted with one or more suitable substituents; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is -(CH 2 )sCH 3 ; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is - (CH 2 ) 7 -C(0)OR x , wherein R x is methyl; R b is hydrogen; R c is hydrogen; R d is hydrogen; R e is hydrogen; R f is -(CH 2 )sCH ; R g is hydrogen; and n is 1.
  • Compounds of Formula I can have structures where X is -OH; R a is - (CH 2 ) 7 -C(0)OR x , wherei x is
  • Specifically preferred embodiments include, but are not limited to, compounds (i)-(xii):
  • R is independently, at each occurrence, selected from the group consisting of hydrogen and a moiety comprising an a- or ⁇ -functionalized epoxide, said a- or ⁇ - functionalization selected from the group consisting of -OH, -SH, and -NHR 23 , wherein at least one R group is a moiety comprising said a- or ⁇ -functionalized epoxide;
  • R 23 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, cycloalkyl, and -C(0)R 27 ;
  • R z/ is selected from the group consisting of -OR , -SR , -NR R , hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
  • R 35 , R 36 , R 37 , and R 3 J 8 O are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl;
  • R', R", R'", R s , and R 1 are each independently, at each occurrence, selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl; y is independently, at each occurrence, an integer selected from 0 to 6; and z is an integer selected from 1 to 20; wherein said alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl are each independently, at each occurrence, substituted or unsubstituted with one or more suitable substituents.
  • R can independently be, at each occurrence, selected from th gen and a moiety of formula:
  • R', R", R'", R s , and R 1 are each
  • Compounds of Formula II can have structures where y is 0 at each occurrence.
  • Compounds of Formula II can have structures where z is an integer selected from 1, 2, 3, 4, 5, or 6. In certain embodiments, z is 3.
  • R', R", and R'" are each hydrogen
  • y is 0 at each occurrence
  • compounds of the invention include compounds prepared from epoxidation of castor oil or a castor oil derivative (e.g., ricinoleic acid, ricinoleic acid methyl ester, glyceryl monoricinoleate, glyceryl diricinoleate).
  • a castor oil derivative e.g., ricinoleic acid, ricinoleic acid methyl ester, glyceryl monoricinoleate, glyceryl diricinoleate.
  • an epoxide of formula (1) can react with a sulfur- based species of formula (2), wherein R 50 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl.
  • R 50 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycle, and cycloalkyl.
  • the resulting thiol or thioether compound (3) can be removed from the medium.
  • the sulfur-based species of formula (2) is hydrogen sulfide (i.e., wherein R is H)
  • the resulting thiol of formula (3) can react with an additional equivalent of epoxide (1) to form a non-volatile mercaptan of formula (4).
  • the unexpected superior scavenging ability of the epoxide compounds disclosed herein is believed to result from intramolecular acid catalyzation of the epoxide by the adjacent a- or ⁇ -functionality, which weakens the epoxide C-0 bond and promotes nucleophilic addition of mercaptans and/or hydrogen sulfide to form an alternate functionality.
  • the a- or ⁇ -functionalization can activate the epoxide for nucleophilic addition by serving as a hydrogen bond donor to the epoxide oxygen atom.
  • a composition of the invention can contain a pure composition of a compound of Formula II.
  • a composition of the invention contains a mixture of two or more structurally distinct compounds of Formula II.
  • a composition of the invention comprises from about 20 to about 100 percent by weight of one or more compounds of the invention, or from about 20 to about 98 percent by weight of one or more compounds of the invention, or from about 50 to 97 percent by weight of one or more compounds of the invention.
  • a composition of the invention comprises about 50 percent by weight of one or more compounds of the invention.
  • compositions of the invention can optionally include one or more additives.
  • Suitable additives include, but are not limited to, asphaltene inhibitors, paraffin inhibitors, corrosion inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, hydrogen sulfide scavengers, gas hydrate inhibitors, biocides, pH modifiers, surfactants, and solvents.
  • Suitable asphaltene inhibitors include, but are not limited to, aliphatic sulphonic acids; alkyl aryl sulphonic acids; aryl sulfonates; lignosulfonates;
  • alkylphenol/aldehyde resins and similar sulfonated resins alkylphenol/aldehyde resins and similar sulfonated resins; polyolefin esters;
  • polyolefin imides polyolefin esters with alkyl, alkylenephenyl or alkylenepyridyl functional groups; polyolefin amides; polyolefin amides with alkyl, alkylenephenyl or alkylenepyridyl functional groups; polyolefin imides with alkyl, alkylenephenyl or alkylenepyridyl functional groups; alkenyl/vinyl pyrrolidone copolymers; graft polymers of polyolefins with maleic anhydride or vinyl imidazole; hyperbranched polyester amides; polyalkoxylated asphaltenes, amphoteric fatty acids, salts of alkyl succinates, sorbitan monooleate, and polyisobutylene succinic anhydride.
  • Paraffin Inhibitors Paraffin Inhibitors
  • Suitable alkyl, hydroxyalkyl, alkylaryl arylalkyl or arylamine quaternary salts include those alkylaryl, arylalkyl and arylamine quaternary salts of the formula [N + R 5a R 6a R 7a R 8a ] [X ⁇ ] wherein R 5a , R 6a , R 7a , and R 8a contain one to 18 carbon atoms, and X is CI, Br or I.
  • R , R , R /a , and R 8a are each independently selected from the group consisting of alkyl (e.g., C -Cn alkyl), hydroxyalkyl (e.g., C C ⁇ hydroxyalkyl), and arylalkyl (e.g., benzyl).
  • the mono or polycyclic aromatic amine salt with an alkyl or alkylaryl halide include salts of the formula [N + R 5a R 6a R 7a R 8a ][X ⁇ ] wherein R 5a , R 6a , R 7a , and R 8a contain one to 18 carbon atoms, and X is CI, Br or I.
  • Suitable quaternary ammonium salts include tetramethyl ammonium chloride, tetraethyl ammonium chloride, tetrapropyl ammonium chloride, tetrabutyl ammonium chloride, tetrahexyl ammonium chloride, tetraoctyl ammonium chloride, benzyltrimethyl ammonium chloride, benzyltriethyl ammonium chloride, phenyltrimethyl ammonium chloride, phenyltriethyl ammonium chloride, cetyl benzyldimethyl ammonium chloride, and hexadecyl trimethyl ammonium chloride.
  • the quaternary ammonium salt is an alkylamine benzyl quaternary ammonium salt, a benzyl triethanolamine quaternary ammonium salt or a benzyl dimethylaminoethanolamine quaternary ammonium salt.
  • the corrosion inhibitor can be a quaternary ammonium or alkyl pyridinium quaternary salt such as those represented by the general formula:
  • R 9a is an alkyl group, an aryl group, or an arylalkyl group, wherein said alkyl groups have from 1 to about 18 carbon atoms and B is CI, Br or I.
  • alkyl pyridinium salts and alkyl pyridinium benzyl quats.
  • Exemplary compounds include methyl pyridinium chloride, ethyl pyridinium chloride, propyl pyridinium chloride, butyl pyridinium chloride, octyl pyridinium chloride, decyl pyridinium chloride, lauryl pyridinium chloride, cetyl pyridinium chloride, benzyl pyridinium and an alkyl benzyl pyridinium chloride, preferably wherein the alkyl is a CrC 6 hydrocarbyl group.
  • the corrosion inhibitor includes benzyl pyridinium chloride.
  • the corrosion inhibitor can be an imidazoline derived from a diamine, such as ethylene diamine (EDA), diethylene triamine (DETA), triethylene tetraamine (TETA) etc. and a long chain fatty acid such as tall oil fatty acid (TOFA).
  • a diamine such as ethylene diamine (EDA), diethylene triamine (DETA), triethylene tetraamine (TETA) etc.
  • TETA triethylene tetraamine
  • TOFA tall oil fatty acid
  • R 12a and R 13a are independently a CrC 6 alkyl group or hydrogen
  • R l la is hydrogen, CrC 6 alkyl, C C 6 hydroxyalkyl, or CrC 6 arylalkyl
  • R 10a is a C C 2 o alkyl or a Ci-C2o alkoxyalkyl group.
  • R l la , R 12a and R 13a are each hydrogen and R 10a is the alkyl mixture typical in tall oil fatty acid (TOFA).
  • the corrosion inhibitor compound can be an imidazolinium compound of the following formula:
  • R 12a and R 13a are independently a C]_-C alkyl group or hydrogen
  • R l la and R 14a are independently hydrogen, C]_-C alkyl, C]_-C hydroxyalkyl, or C]_-C
  • R 10 is a C C ⁇ alkyl or a C C 2 o alkoxyalkyl group.
  • Suitable mono-, di-and trialkyl as well as alkylaryl phosphate esters and phosphate esters of mono, di, and triethanolamine typically contain between from 1 to about 18 carbon atoms.
  • Preferred mono-, di-and trialkyl phosphate esters, alkylaryl or arylalkyl phosphate esters are those prepared by reacting a C 3 -C 18 aliphatic alcohol with phosphorous pentoxide. The phosphate intermediate interchanges its ester groups with triethyl phosphate with triethylphosphate producing a more broad distribution of alkyl phosphate esters.
  • the phosphate ester can be made by admixing with an alkyl diester, a mixture of low molecular weight alkyl alcohols or diols.
  • the low molecular weight alkyl alcohols or diols preferably include C 6 to C 10 alcohols or diols.
  • the corrosion inhibitor compound can further be a monomeric or oligomeric fatty acid. Preferred are C 14 -C22 saturated and unsaturated fatty acids as well as dimer, trimer and oligomer products obtained by polymerizing one or more of such fatty acids. d. Scale Inhibitors
  • Suitable scale inhibitors include, but are not limited to, phosphates, phosphate esters, phosphoric acids, phosphonates, phosphonic acids,
  • polyacrylamides salts of acrylamido-methyl propane sulfonate/acrylic acid copolymer (AMPS/AA), phosphinated maleic copolymer (PHOS/MA), and salts of a polymaleic acid/acrylic acid/acrylamido-methyl propane sulfonate terpolymer (PMA/AMPS).
  • AMPS/AA acrylamido-methyl propane sulfonate/acrylic acid copolymer
  • PHOS/MA phosphinated maleic copolymer
  • PMA/AMPS polymaleic acid/acrylic acid/acrylamido-methyl propane sulfonate terpolymer
  • Suitable emulsifiers include, but are not limited to, salts of carboxylic acids, products of acylation reactions between carboxylic acids or carboxylic anhydrides and amines, and alkyl, acyl and amide derivatives of saccharides (alkyl- saccharide emulsifiers). f. Water Clarifiers
  • Suitable water clarifiers include, but are not limited to, inorganic metal salts such as alum, aluminum chloride, and aluminum chlorohydrate, or organic polymers such as acrylic acid based polymers, acrylamide based polymers, polymerized amines, alkanolamines, thiocarbamates, and cationic polymers such as diallyldimethylammonium chloride(D ADM AC) .
  • inorganic metal salts such as alum, aluminum chloride, and aluminum chlorohydrate
  • organic polymers such as acrylic acid based polymers, acrylamide based polymers, polymerized amines, alkanolamines, thiocarbamates, and cationic polymers such as diallyldimethylammonium chloride(D ADM AC) .
  • D ADM AC diallyldimethylammonium chloride
  • Suitable dispersants include, but are not limited to, aliphatic phosphonic acids with 2-50 carbons, such as hydroxyethyl diphosphonic acid, and aminoalkyl phosphonic acids, e.g. polyaminomethylene phosphonates with 2-10 N atoms e.g. each bearing at least one methylene phosphonic acid group; examples of the latter are ethylenediamine tetra(methylene phosphonate), diethylenetriamine penta(methylene phosphonate) and the triamine- and tetramine-polymethylene phosphonates with 2-4 methylene groups between each N atom, at least 2 of the numbers of methylene groups in each phosphonate being different.
  • Other suitable dispersion agents include lignin or derivatives of lignin such as lignosulfonate and naphthalene sulfonic acid and derivatives. h. Emulsion Breakers
  • Suitable emulsion breakers include, but are not limited to,
  • DBSA dodecylbenzylsulfonic acid
  • NAXSA sodium salt of xylenesulfonic acid
  • resins such as phenolic and epoxide resins.
  • Suitable additional hydrogen sulfide scavengers include, but are not limited to, oxidants (e.g., inorganic peroxides such as sodium peroxide, or chlorine dioxide), aldehydes (e.g., of 1-10 carbons such as formaldehyde or glutaraldehyde or (meth) acrolein), triazines (e.g., monoethanol amine triazine, monomethylamine triazine, and triazines from multiple amines or mixtures thereof), and glyoxal.
  • oxidants e.g., inorganic peroxides such as sodium peroxide, or chlorine dioxide
  • aldehydes e.g., of 1-10 carbons such as formaldehyde or glutaraldehyde or (meth) acrolein
  • triazines e.g., monoethanol amine triazine, monomethylamine triazine, and triazines from multiple amines or mixture
  • Suitable gas hydrate inhibitors include, but are not limited to,
  • thermodynamic hydrate inhibitors include, but are not limited to, NaCl salt, KC1 salt, CaCl 2 salt, MgCl 2 salt, NaBr 2 salt, formate brines (e.g.
  • polyols such as glucose, sucrose, fructose, maltose, lactose, gluconate, monoethylene glycol, diethylene glycol, triethylene glycol, mono-propylene glycol, dipropylene glycol, tripropylene glycols, tetrapropylene glycol, monobutylene glycol, dibutylene glycol, tributylene glycol, glycerol, diglycerol, triglycerol, and sugar alcohols (e.g.
  • Suitable kinetic hydrate inhibitors and anti-agglomerates include, but are not limited to, polymers and copolymers, polysaccharides (such as hydroxy-ethylcellulose (HEC), carboxymethylcellulose (CMC), starch, starch derivatives, and xanthan), lactams (such as
  • polyvinylcaprolactam polyvinyl lactam
  • pyrrolidones such as polyvinyl pyrrolidone of various molecular weights
  • surfactants such as fatty acid salts, ethoxylated alcohols, propoxylated alcohols, sorbitan esters, ethoxylated sorbitan esters, polyglycerol esters of fatty acids, alkyl glucosides, alkyl polyglucosides, alkyl sulfates, alkyl sulfonates, alkyl ester sulfonates, alkyl aromatic sulfonates, alkyl betaine, alkyl amido betaines), hydrocarbon based dispersants (such as lignosulfonates, iminodisuccinates, polyaspartates), amino acids, and proteins. k. Biocides
  • Suitable biocides include, but are not limited to, oxidizing and non- oxidizing biocides.
  • Suitable non-oxidizing biocides include, for example, aldehydes (e.g., formaldehyde, glutaraldehyde, and acrolein), amine-type compounds (e.g., quaternary amine compounds and cocodiamine), halogenated compounds (e.g., bronopol and 2-2-dibromo-3-nitrilopropionamide (DBNPA)), sulfur compounds (e.g., isothiazolone, carbamates, and metronidazole), and quaternary phosphonium salts (e.g., tetrakis(hydroxymethyl)phosphonium sulfate (THPS)).
  • aldehydes e.g., formaldehyde, glutaraldehyde, and acrolein
  • amine-type compounds e.g., quaternary
  • Suitable oxidizing biocides include, for example, sodium hypochlorite, trichloroisocyanuric acids, dichloroisocyanuric acid, calcium hypochlorite, lithium hypochlorite, chlorinated hydantoins, stabilized sodium hypobromite, activated sodium bromide, brominated hydantoins, chlorine dioxide, ozone, and peroxides.
  • Suitable pH modifiers include, but are not limited to, alkali hydroxides, alkali carbonates, alkali bicarbonates, alkaline earth metal hydroxides, alkaline earth metal carbonates, alkaline earth metal bicarbonates and mixtures or combinations thereof.
  • Exemplary pH modifiers include NaOH, KOH, Ca(OH) 2 , CaO, Na 2 C0 3 , KHC0 3 , K 2 C0 3 , NaHC0 3 , MgO, and Mg(OH) 2 .
  • Suitable surfactants include, but are not limited to, anionic surfactants, cationic surfactants, zwitterionic surfactants, and nonionic surfactants.
  • Anionic surfactants include alkyl aryl sulfonates, olefin sulfonates, paraffin sulfonates, alcohol sulfates, alcohol ether sulfates, alkyl carboxylates and alkyl ether carboxylates, and alkyl and ethoxylated alkyl phosphate esters, and mono and dialkyl sulfosuccinates and sulfosuccinamates.
  • Cationic surfactants include alkyl trimethyl quaternary ammonium salts, alkyl dimethyl benzyl quaternary ammonium salts, dialkyl dimethyl quaternary ammonium salts, and imidazolinium salts.
  • Nonionic surfactants include alcohol alkoxylates, alkylphenol alkoxylates, block copolymers of ethylene, propylene and butylene oxides, alkyl dimethyl amine oxides, alkyl-bis(2-hydroxyethyl) amine oxides, alkyl amidopropyl dimethyl amine oxides, alkylamidopropyl-bis(2-hydroxyethyl) amine oxides, alkyl polyglucosides, polyalkoxylated glycerides, sorbitan esters and polyalkoxylated sorbitan esters, and alkoyl polyethylene glycol esters and diesters.
  • amphoteric surfactants such as alkyl amphoacetates and amphodiacetates, alkyl amphopropripionates and amphodipropionates, and alkyliminodiproprionate.
  • the surfactant can be a quaternary ammonium compound, an amine oxide, an ionic or non-ionic surfactant, or any combination thereof.
  • Suitable quaternary amine compounds include, but are not limited to, alkyl benzyl ammonium chloride, benzyl cocoalkyl(C 1 2-C 1 8)dimethylammonium chloride, dicocoalkyl (C 1 2-C 1 g)dimethylammonium chloride, ditallow dimethylammonium chloride, di(hydrogenated tallow alkyl)dimethyl quaternary ammonium methyl chloride, methyl bis(2-hydroxyethyl cocoalkyliCn-Cis) quaternary ammonium chloride, dimethyl(2-ethyl) tallow ammonium methyl sulfate, n- dodecylbenzyldimethylammonium chloride, n-octadecylbenzyldimethyl ammonium chlor
  • the surfactant is cocodimethyl amine oxide.
  • the cocodimethyl amine oxide can be present in the composition in an amount ranging from about 0.1 wt % to about 30 wt , or about 1 wt % to about 20 wt %.
  • the cocodimethyl amine oxide is present in the composition in an amount of 3 wt %.
  • the cocodimethyl amine oxide can enhance scavenging ability of compounds of the invention. n. Solvents
  • Suitable solvents include, but are not limited to, alcohols, hydrocarbons, ketones, ethers, aromatics, amides, nitriles, sulfoxides, esters, and aqueous systems.
  • the solvent is water, isopropanol, methanol, ethanol, 2- ethylhexanol, heavy aromatic naphtha, toluene, ethylene glycol, ethylene glycol monobutyl ether (EGMBE), diethylene glycol monoethyl ether, or xylene.
  • Representative polar solvents suitable for formulation with the composition include water, brine, seawater, alcohols (including straight chain or branched aliphatic such as methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, hexanol, octanol, decanol, 2-butoxyethanol, etc.), glycols and derivatives (ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, ethylene glycol monobutyl ether, etc.), ketones (cyclohexanone, diisobutylketone), N-methylpyrrolidinone (NMP), N,N- dimethylformamide and the like.
  • alcohols including straight chain or branched aliphatic such as methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, hexanol, octanol, decano
  • non-polar solvents suitable for formulation with the composition include aliphatics such as pentane, hexane, cyclohexane, methylcyclohexane, heptane, decane, dodecane, diesel, and the like; aromatics such as toluene, xylene, heavy aromatic naphtha, fatty acid derivatives (acids, esters, amides), and the like.
  • the solvent can be a polyhydroxylated solvent, a polyether, an alcohol, or a combination thereof.
  • the solvent can be monoethyleneglycol, methanol, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), tetrahydrofuran (THF), or a combination thereof.
  • DMSO dimethyl sulfoxide
  • DMF dimethylformamide
  • THF tetrahydrofuran
  • the solvent can be methyl carbitol (also referred to as 2-(2- methoxyethoxy) ethanol).
  • a composition of the invention can comprise from 0 to about 80 percent by weight of one or more solvents, based on the weight of the composition.
  • a composition of the invention can comprise from 0 to about 50 percent by weight of one or more solvents, based on the weight of the composition.
  • a composition of the invention can comprise 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, or 60% by weight of one or more solvents, based on the weight of the composition. o. Additional Components
  • compositions made according to the invention can further include additional functional agents or additives that provide a beneficial property.
  • Additional agents or additives will vary according to the particular scavenging composition being manufactured and its intended use as one skilled in the art will appreciate. According to one embodiment, the scavenging compositions do not contain any of the additional agents or additives.
  • a scavenging compound or composition of the invention can be commercially available. Alternatively, a scavenging compound or composition of the invention can be prepared via one or more synthetic steps.
  • a scavenging compound or composition of the invention can be prepared by treating an olefin with an epoxidation reagent (e.g., meta-chloroperoxybenzoic acid).
  • an epoxidation reagent e.g., meta-chloroperoxybenzoic acid
  • a scavenging compound or composition of the invention can be prepared by intramolecular cyclization of a halohydrin.
  • a-Functionalized epoxides of formula (5) can be prepared as described in Scheme 3, wherein R a -R e are as defined above.
  • ⁇ -Functionalized epoxides of formula (8) can be prepared as described in Scheme 4, wherein R a -R g are as defined above.
  • ⁇ -Functionalized epoxides of formula (10) can be prepared as described in Scheme 5, wherein R a -R c are as defined above, R d and R f together with the carbon atoms to which they are attached form an aryl, and R e and R g are absent.
  • Treatment of an alkene of formula (11) with a solution of hydrogen peroxide (7) (e.g., 5-70% H 2 0 2 solution), preferably at 25-40 °C and for 1 to 24 hours, will provide an epoxide of formula (10).
  • Compounds of the invention can be prepared from castor oil or a castor oil derivative (e.g., a glyceryl ricinoleate) through epoxidation with performic acid generated in situ.
  • a castor oil derivative e.g., a glyceryl ricinoleate
  • the mixture is heated to 40 °C with stirring followed by dropwise addition of 2 equivalents of hydrogen peroxide (30% aq. H 2 O 2 ).
  • the mixture is then allowed to react for 16 to 18 hours at 40 °C. After the reaction, the mixture is washed twice with 5% NaHC0 3 solution.
  • the product is further purified by vacuum distillation.
  • non-viscous substrates e.g. castor oil methyl ester
  • further purification can be carried out by centrifugation to remove residual water followed by drying with anhydrous Na 2 S0 4 .
  • Castor oil and its derivatives give clear viscous to slightly viscous products.
  • FTIR and NMR analysis of the purified product confirms quantitative reaction of the carbon-carbon double bonds.
  • the appearance of bands at 827 and 840 cm "1 in FTIR spectra of the product supported by the appearance of new signals at 2.8 to 3.2 ppm in 1H NMR confirms epoxidation of the double bonds.
  • the compounds can be further modified, for example, by manipulation of substituents. These manipulations can include, but are not limited to, reduction, oxidation, organometallic cross-coupling, alkylation, acylation, and hydrolysis reactions which are commonly known to those skilled in the art. In some cases, the order of carrying out the foregoing reaction schemes can be varied to facilitate the reaction or to avoid unwanted reaction products. 5. Methods of Use
  • the compounds and compositions of the invention can be used for sweetening a gas or liquid, such as a sour gas or a sour liquid.
  • the compounds and compositions can be used for scavenging hydrogen sulfide and/or mercaptans from a gas or liquid stream by treating said stream with an effective amount of a compound or composition of the invention, as described herein.
  • the compounds and compositions of the invention can be used in any industry where it is desirable to capture hydrogen sulfide and/or mercaptans from a gas or liquid stream.
  • the compounds and compositions can be used in water systems, condensate/oil systems/gas systems, or any combination thereof.
  • the compounds and compositions can be applied to a gas or liquid produced or used in the production, transportation, storage, and/or separation of crude oil or natural gas.
  • the compounds and compositions can be applied to a gas stream used or produced in a coal-fired process, such as a coal-fired power plant.
  • the compounds and compositions can be applied to a gas or liquid produced or used in a waste-water process, a farm, a slaughter house, a land-fill, a municipality waste-water plant, a coking coal process, or a biofuel process.
  • the compounds and compositions can be added to any fluid or gas containing hydrogen sulfide and/or a mercaptan, or a fluid or gas that can be exposed to hydrogen sulfide and/or a mercaptan.
  • a fluid to which the compounds and compositions can be introduced can be an aqueous medium.
  • the aqueous medium can comprise water, gas, and optionally liquid hydrocarbon.
  • a fluid to which the compounds and compositions can be introduced can be a liquid hydrocarbon.
  • the liquid hydrocarbon can be any type of liquid hydrocarbon including, but not limited to, crude oil, heavy oil, processed residual oil, bitminous oil, coker oils, coker gas oils, fluid catalytic cracker feeds, gas oil, naphtha, fluid catalytic cracking slurry, diesel fuel, fuel oil, jet fuel, gasoline, and kerosene.
  • the gas can be a sour gas.
  • the fluid or gas can be a refined hydrocarbon product.
  • a fluid or gas treated with a compound or composition of the invention can be at any selected temperature, such as ambient temperature or an elevated temperature.
  • the fluid (e.g., liquid hydrocarbon) or gas can be at a temperature of from about 40 °C to about 250 °C.
  • the fluid or gas can be at a temperature of from -50 °C to 300 °C, 0 °C to 200 °C, 10 °C to 100 °C, or 20 °C to 90 °C.
  • the fluid or gas can be at a temperature of 22 °C, 23 °C, 24 °C, 25°C, 26 °C, 27 °C, 28 °C, 29 °C, 30 °C, 31 °C, 32 °C, 33 °C, 34 °C, 35 °C, 36 °C, 37 °C, 38 °C, 39 °C, or 40 °C.
  • the fluid or gas can be at a temperature of 85 °C, 86 °C, 87 °C, 88 °C, 89 °C, 90 °C, 91 °C, 92 °C, 93 °C, 94 °C, 95 °C, 96 °C, 97 °C, 98 °C, 99 °C, or 100 °C.
  • the compounds and compositions of the invention can be added to a fluid at various levels of water cut.
  • the water cut can be from 0% to 100% volume/volume (v/v), from 1% to 80% v/v, or from 1% to 60% v/v.
  • the fluid can be an aqueous medium that contains various levels of salinity.
  • the fluid can have a salinity of 0% to 25%, about 1% to 24%, or about 10% to 25% weight/weight (w/w) total dissolved solids (TDS).
  • the fluid or gas in which the compounds and compositions of the invention are introduced can be contained in and/or exposed to many different types of apparatuses.
  • the fluid or gas can be contained in an apparatus that transports fluid or gas from one point to another, such as an oil and/or gas pipeline.
  • the apparatus can be part of an oil and/or gas refinery, such as a pipeline, a separation vessel, a dehydration unit, or a gas line.
  • the fluid can be contained in and/or exposed to an apparatus used in oil extraction and/or production, such as a wellhead.
  • the apparatus can be part of a coal-fired power plant.
  • the apparatus can be a scrubber (e.g., a wet flue gas desulfurizer, a spray dry absorber, a dry sorbent injector, a spray tower, a contact or bubble tower, or the like).
  • the apparatus can be a cargo vessel, a storage vessel, a holding tank, or a pipeline connecting the tanks, vessels, or processing units.
  • the fluid or gas can be contained in water systems, condensate/oil systems/gas systems, or any combination thereof.
  • the compounds or compositions of the invention can be introduced into a fluid or gas by any appropriate method for ensuring dispersal of the scavenger through the fluid or gas.
  • the compounds and compositions can be injected using mechanical equipment such as chemical injection pumps, piping tees, injection fittings, atomizers, quills, and the like.
  • the compounds and compositions of the invention can be introduced with or without one or more additional polar or non- polar solvents depending upon the application and requirements.
  • the compounds and compositions of the invention can be pumped into an oil and/or gas pipeline using an umbilical line. Capillary injection systems can be used to deliver the compounds and compositions to a selected fluid.
  • the compounds and compositions can be introduced into a liquid and mixed.
  • the compounds and compositions can be injected into a gas stream as an aqueous or nonaqueous solution, mixture, or slurry.
  • the fluid or gas can be passed through an absorption tower comprising a compound or composition of the invention.
  • the compounds and compositions can be applied to a fluid or gas to provide any selected scavenger concentration.
  • the compounds and compositions can be applied to a fluid or gas to provide a scavenger concentration of about 1 parts per million (ppm) to about 1,000,000 ppm, about 1 parts per million (ppm) to about 100,000 ppm, about 10 ppm to about 75,000 ppm, about 100 ppm to about 45,000 ppm, about 500 ppm to about 40,000 ppm, about 1,000 ppm to about 35,000 ppm, about 3,000 ppm to about 30,000 ppm, about 4,000 ppm to about 25,000 ppm, about 5,000 ppm to about 20,000 ppm, about 6,000 ppm to about 15,000 ppm, or about 7,000 ppm to about 10,000 ppm.
  • the compounds and compositions can be applied to a fluid at a concentration of about 100 ppm to about 10,000 ppm, about 200 ppm to about 8,000 ppm, or about 500 ppm to about 6,000 ppm.
  • the compounds and compositions are applied to a fluid or gas to provide a scavenger concentration of 3,000 ppm or greater, 3,500 ppm or greater, 4,000 ppm or greater, 4,500 ppm or greater, or 5,000 ppm or greater.
  • Each system can have its own requirements, and a more sour gas (e.g., containing more hydrogen sulfide) can require a higher dose rate of a compound or composition of the invention.
  • the compounds and compositions can be applied to a fluid or gas in an equimolar amount or greater relative to hydrogen sulfide and/or mercaptans present in the fluid or gas.
  • the compounds and compositions can be applied to a fluid or gas to provide a scavenger to hydrogen sulfide and/or mercaptans molar ratio of 1: 1, 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, or 10: 1.
  • the compounds and compositions can be applied to a fluid or gas as a neat composition (e.g., the compounds and compositions can be used neat in a contact tower).
  • the hydrogen sulfide and/or mercaptan in a fluid or gas can be reduced by any amount by treatment with a compound or composition of the invention.
  • the actual amount of residual hydrogen sulfide and/or mercaptan after treatment can vary depending on the starting amount.
  • the hydrogen sulfide and/or mercaptan levels can be reduced to about 150 ppm by volume or less, as measured in the vapor phase, based on the volume of the liquid media.
  • the hydrogen sulfide levels and/or mercaptan can be reduced to 100 ppm by volume or less, as measured in the vapor phase, based on the volume of the liquid media.
  • the hydrogen sulfide and/or mercaptan levels can be reduced to 50 ppm by volume or less, as measured in the vapor phase, based on the volume of the liquid media.
  • the hydrogen sulfide and/or mercaptan levels can be reduced to 20 ppm by volume or less, as measured in the vapor phase, based on the volume of the liquid media.
  • the hydrogen sulfide and/or mercaptan levels can be reduced to 15 ppm by volume or less, as measured in the vapor phase, based on the volume of the liquid media.
  • the hydrogen sulfide and/or mercaptan levels can be reduced to 10 ppm by volume or less, as measured in the vapor phase, based on the volume of the liquid media.
  • the hydrogen sulfide and/or mercaptan levels can be reduced to 5 ppm by volume or less, as measured in the vapor phase, based on the volume of the liquid media.
  • the hydrogen sulfide and/or mercaptan levels can be reduced to 0 ppm by volume, as measured in the vapor phase, based on the volume of the liquid media.
  • Example 2 can be prepared by epoxidation of l-buten-4-ol (e.g., with a 5- 70% H 2 0 2 solution at 25-40 °C for 1 to 24 hours).
  • Example 3 can be prepared by epoxidation of l-octen-3-ol (e.g., with a 5- 70% H 2 0 2 solution at 25-40 °C for 1 to 24 hours).
  • Example 4 can be prepared by epoxidation of l-octen-4-ol (e.g., with a 5- 70% H 2 0 2 solution at 25-40 °C for 1 to 24 hours).
  • Example 5 can be prepared by epoxidation of 3-penten-2-ol (e.g., with a 5-70% H 2 0 2 solution at 25-40 °C for 1 to 24 hours).
  • Example 6 can be prepared by epoxidation of 3-penten-l-ol (e.g., with a 5-70% H 2 0 2 solution at 25-40 °C for 1 to 24 hours).
  • Example 7 can be prepared by epoxidation of 2-vinylphenol (e.g., with a 5-70% H 2 0 2 solution at 25-40 °C for 1 to 24 hours)
  • Example 9 can be prepared by epoxidation of ricinoleic acid methyl ester with performic acid generated in situ.
  • 0.5 equivalent of formic acid is added to 1 equivalent of the substrate in a round bottom flask.
  • the mixture is heated to 40 °C with stirring followed by dropwise addition of 2 equivalents of hydrogen peroxide (30% aq. H 2 0 2 ).
  • the mixture is then allowed to react for 16 to 18 hours at 40 °C. After the reaction, the mixture is washed twice with 5% NaHC0 3 solution.
  • the product is further purified by vacuum distillation.
  • non-viscous substrates e.g.
  • castor oil methyl ester further purification can be carried out by centrifugation to remove residual water followed by drying with anhydrous Na 2 S0 4 .
  • Castor oil and its derivatives give clear viscous to slightly viscous products.
  • FTIR and NMR analysis of the purified product confirms quantitative reaction of the carbon-carbon double bond.
  • Example 10 can be prepared by epoxidation of a glyceryl monoricinoleate with performic acid generated in situ.
  • a typical synthesis 0.5 equivalent of formic acid is added to 1 equivalent of the substrate in a round bottom flask. The mixture is heated to 40 °C with stirring followed by dropwise addition of 2 equivalents of hydrogen peroxide (30% aq. H 2 0 2 ). The mixture is then allowed to react for 16 to 18 hours at 40 °C. After the reaction, the mixture is washed twice with 5% NaHC0 3 solution.
  • the product is further purified by vacuum distillation.
  • non-viscous substrates e.g.
  • Example 12 can be prepared by epoxidation of castor oil with performic acid generated in situ.
  • 0.5 equivalent of formic acid is added to 1 equivalent of the substrate in a round bottom flask.
  • the mixture is heated to 40 °C with stirring followed by dropwise addition of 2 equivalents of hydrogen peroxide (30% aq. H 2 0 2 ).
  • the mixture is then allowed to react for 16 to 18 hours at 40 °C.
  • the mixture is washed twice with 5% NaHC0 3 solution.
  • the product is further purified by vacuum distillation.
  • non-viscous substrates e.g. castor oil methyl ester
  • further purification can be carried out by centrifugation to remove residual water followed by drying with anhydrous Na 2 S0 4 .
  • Castor oil and its derivatives give clear viscous to slightly viscous products.
  • FTIR and NMR analysis of the purified product confirms quantitative reaction of the carbon-carbon double bonds.
  • the appearance of bands at 827 and 840 cm "1 in FTIR spectra of the product supported by the appearance of new signals at 2.8 to 3.2 ppm in 1H NMR confirms epoxidation of the double bonds.
  • Figure 1 shows the dose response profile of glycidol when used to scavenge 1 -propyl mercaptan from kerosene.
  • the test was conducted using kerosene samples containing 1,000 ppm of 1 -propyl mercaptan. The samples were dosed with different amounts of glycidol (0-5,000 ppm). Glycidol was added to each bottle followed by the kerosene containing the mercaptan. The amount of mercaptan in the vapor was measured using a 200 mL full 500 mL container using Draeger or Gastec Tubes to measure the amount of mercaptan in the vapor. The samples were vigorously shaken for 30 seconds and then set at room temperature for 18-24 hours. After 18-24 hours, the sample was shaken vigorously for 30 seconds and then tested with a Draeger or Gastec tube.
  • Figure 1 demonstrates that when a kerosene sample containing 1 -propyl mercaptan sample is treated with a scavenger, glycidol, it is possible to decrease the vapor phase detectable mercaptan with increasing amounts of scavenger.
  • a scavenger glycidol
  • Figure 2 shows the dose response profile of glycidol when used to scavenge a 1,000 ppm mixture of mercaptans (22% 1 -propyl mercaptan, 22% 2- propyl mercaptan, 43% butyl mercaptan, 11% benzyl thiol, 2% ethane thiol) in kerosene at 22 °C.
  • the amount of mercaptan in the vapor was measured using a 200 mL full 500 mL container using Draeger or Gastec Tubes to measure the amount of mercaptan in the vapor. Glycidol was added to the bottle followed by the kerosene containing the mercaptan.
  • Figure 3 shows the dose response profile of glycidol when used to scavenge a 1,000 ppm mixture of mercaptans (22% 1 -propyl mercaptan, 22% 2- propyl mercaptan, 43% butyl mercaptan, 11% benzyl thiol, 2% ethane thiol) in kerosene at 22 °C.
  • the scavenger was evaluated at a ratio of 1 equivalent scavenger to 1 equivalent mercaptan ("1: 1"); 3 equivalents scavenger to 1 equivalent mercaptan ("3: 1"); and 5 equivalents scavenger to 1 equivalent mercaptan ("5: 1").
  • the scavenger was evaluated in the absence of 3% cocodimethylamine oxide surfactant ("unpromoted"), and in the presence of 3% cocodimethylamine oxide surfactant ("promoted”).
  • the results indicate that scavenger : mercaptan ratios of 3: 1 and 5: 1 effectively removes mercaptan species from the kerosene, even in the absence of the cocodimethylamine oxide promoter.
  • formulations with a surfactant e.g., cocodimethylamine oxide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Environmental & Geological Engineering (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés de capture et des compositions utiles dans des applications se rapportant à la production, le transport, l'entreposage et la séparation de pétrole brut et de gaz naturel. L'invention concerne également des procédés d'utilisation des composés et des compositions en tant que capteurs, en particulier dans des applications associées à la production, au transport, à l'entreposage et à la séparation de pétrole brut et de gaz naturel.
PCT/US2014/044114 2013-06-27 2014-06-25 Capteurs de sulfure d'hydrogène à base d'époxyde WO2014210166A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361840338P 2013-06-27 2013-06-27
US61/840,338 2013-06-27

Publications (1)

Publication Number Publication Date
WO2014210166A1 true WO2014210166A1 (fr) 2014-12-31

Family

ID=52114557

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/044114 WO2014210166A1 (fr) 2013-06-27 2014-06-25 Capteurs de sulfure d'hydrogène à base d'époxyde

Country Status (2)

Country Link
US (1) US9719030B2 (fr)
WO (1) WO2014210166A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016154029A1 (fr) * 2015-03-20 2016-09-29 Massachusetts Institute Of Technology Formation de macromolécules par croissance itérative et composés associés
CN108430603A (zh) * 2016-01-05 2018-08-21 多尔夫凯塔尔化学制品（I）私人有限公司 硫化氢清除用添加剂组合物及其使用方法

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015191064A1 (fr) * 2014-06-11 2015-12-17 Halliburton Energy Services, Inc. Composition de consolidation pour le traitement de formations souterraines
WO2016093800A1 (fr) * 2014-12-09 2016-06-16 Halliburton Energy Services, Inc. Composition comprenant un ester de glycérol comprenant au moins deux époxydes pour le traitement de formations souterraines
EP3252129B1 (fr) 2015-01-29 2019-08-14 Kuraray Co., Ltd. Composition pour l'élimination de composés soufrés
CN105112093B (zh) * 2015-02-13 2017-01-18 濮阳市联众兴业化工有限公司 一种裂解碳五脱硫方法
AU2016261036B2 (en) 2015-05-14 2019-10-17 Clariant International Ltd Composition and method for scavenging sulfides and mercaptans
DK3400089T3 (da) * 2016-01-08 2022-11-21 Ecolab Usa Inc Multifunktionelt produkt med hydrogensulfidfjernelses- og hydrathæmningsevne
CN109420410B (zh) * 2017-08-22 2021-11-09 中国石油化工股份有限公司 一种高效脱除酸性混合气中有机硫的吸收剂

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6242618B1 (en) * 2000-03-21 2001-06-05 The Lubrizol Corporation H2S scavengers for polysulfide products and methods for scavenging H2S from polysulfide products
US20040086443A1 (en) * 2000-10-13 2004-05-06 Schield John A. Hydrogen sulfide abatement in molten sulfur
US20070142244A1 (en) * 2004-02-11 2007-06-21 Schield John A Hydrocarbons having reduced levels of mercaptans and method and composition useful for preparing same
US8172952B2 (en) * 2007-02-21 2012-05-08 Clearwater International, Llc Reduction of hydrogen sulfide in water treatment systems or other systems that collect and transmit bi-phasic fluids
US20120152857A1 (en) * 2010-12-20 2012-06-21 Baker Hughes Incorporated Non-Nitrogen Sulfide Sweeteners

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2862804A (en) * 1955-12-21 1958-12-02 Gloria Oil And Gas Company Process for sweetening and stabilizing hydrocarbons with an organic epoxide and an aqueous alkaline phenol
US4421733A (en) 1982-05-24 1983-12-20 Shell Oil Company Method of removing hydrogen sulfide from gases utilizing a stabilized metal chelate solution
US4569766A (en) 1984-06-06 1986-02-11 The Standard Oil Company Hydrogen sulfide and mercaptan scavenger
US4680127A (en) 1985-12-13 1987-07-14 Betz Laboratories, Inc. Method of scavenging hydrogen sulfide
NZ223528A (en) 1987-02-19 1991-08-27 Dow Chemical Co Process and scrubbing solution for removal of h 2 s and/or co 2 from gas streams
US5225103A (en) 1989-08-23 1993-07-06 Hoechst Aktiengesellschaft Aqueous aldehyde solutions for trapping hydrogen sulfide in natural gas and crude oil producing plants
US5128049A (en) 1991-01-22 1992-07-07 Gatlin Larry W Hydrogen sulfide removal process
US5552060A (en) * 1995-05-05 1996-09-03 Baker Hughes Incorporated Abatement of hydrogen sulfide with epoxides
US5674377A (en) 1995-06-19 1997-10-07 Nalco/Exxon Energy Chemicals, L.P. Method of treating sour gas and liquid hydrocarbon
NO982505L (no) 1997-06-04 1998-12-07 Nalco Exxon Energy Chem Lp Sammensetning og fremgangsmÕte for avsvovling av gassformige eller flytende hydrokarboner, vandige systemer og blandinger derav
GB0031710D0 (en) 2000-12-27 2001-02-07 Dyno Oil Field Chemicals Process for the reduction or elimination of hydrogen sulphide
US8562820B2 (en) 2001-11-09 2013-10-22 Clearwater International, L.L.C. Sulfide scavenger
US7216710B2 (en) 2004-02-04 2007-05-15 Halliburton Energy Services, Inc. Thiol/aldehyde corrosion inhibitors
US9708547B2 (en) 2007-10-15 2017-07-18 Baker Hughes Incorporated Water-based formulation of H2S/mercaptan scavenger for fluids in oilfield and refinery applications
US20120012507A1 (en) 2010-07-14 2012-01-19 Compton Dennis R Use of alpha-amino ethers for the removal of hydrogen sulfide from hydrocarbons
US9260669B2 (en) 2011-03-24 2016-02-16 Baker Hughes Incorporated Synergistic H2S/mercaptan scavengers using glyoxal

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6242618B1 (en) * 2000-03-21 2001-06-05 The Lubrizol Corporation H2S scavengers for polysulfide products and methods for scavenging H2S from polysulfide products
US20040086443A1 (en) * 2000-10-13 2004-05-06 Schield John A. Hydrogen sulfide abatement in molten sulfur
US20070142244A1 (en) * 2004-02-11 2007-06-21 Schield John A Hydrocarbons having reduced levels of mercaptans and method and composition useful for preparing same
US8172952B2 (en) * 2007-02-21 2012-05-08 Clearwater International, Llc Reduction of hydrogen sulfide in water treatment systems or other systems that collect and transmit bi-phasic fluids
US20120152857A1 (en) * 2010-12-20 2012-06-21 Baker Hughes Incorporated Non-Nitrogen Sulfide Sweeteners

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016154029A1 (fr) * 2015-03-20 2016-09-29 Massachusetts Institute Of Technology Formation de macromolécules par croissance itérative et composés associés
US10125124B2 (en) 2015-03-20 2018-11-13 Massachusetts Institute Of Technology Formation of macromolecules using iterative growth and related compounds
CN108430603A (zh) * 2016-01-05 2018-08-21 多尔夫凯塔尔化学制品（I）私人有限公司 硫化氢清除用添加剂组合物及其使用方法

Also Published As

Publication number Publication date
US9719030B2 (en) 2017-08-01
US20150001132A1 (en) 2015-01-01

Similar Documents

Publication Publication Date Title
US10703710B2 (en) Hydrogen sulfide scavengers
US9719030B2 (en) Epoxide-based hydrogen sulfide scavengers
EP3491106B1 (fr) Compositions antiencrassement et de piégeage du sulfure d'hydrogène
AU2016250539B2 (en) Development of a novel high temperature stable scavenger for removal of hydrogen sulfide
AU2014296417B2 (en) Organic disulfide based corrosion inhibitors
EP3519535B1 (fr) Méthode de traitement du sulfure d'hydrogène dans un courant
US11499108B2 (en) Complete removal of solids during hydrogen sulfide scavenging operations using a scavenger and a Michael acceptor
WO2017192514A1 (fr) Dérivés de 2-mercaptobenzimidazole utilisés en tant qu'inhibiteurs de corrosion
US10538710B2 (en) Hydrogen sulfide scavengers

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14816948

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14816948

Country of ref document: EP

Kind code of ref document: A1